Process of producing keto compounds.



UNITED STATES PATENT OFFICE.

GEORG MERLING, F ELBERFELD, AND HUGO 'RoHLER, or LEVERKUSEN, NEAR oo- LOGNE, GERMANY, ASSIGNORS 'ro FAR-BENFABRIKEN voRM. ERIEDR. BAYER & 00., 0F ELBERFELD, GERMANY, A CORPORATION OF GERMANY.

PROCESS OF PRODUCING KETO COMPOUNDS.

No Drawing. Original application filed October 8, 1912, Serial No. 724,635. Divided and this filed November 13, 1912. Serial No. 731,142.

T 0 0. 1 10720221 2'2 may concern Be it known that we, Gizonc MERLING and Hum KoHLER, doctors of philosophy, chemists, citizens of the German Empire, residing, respectively, at Elberfeld and Leverkusen, near Cologne. Germany, have invented new and useful Improvements in Processes of Producing Keto Compounds, of which the following is a specification,

The present invention concerns the production of keto compounds containing the radical a which have proved to be valuable interme- ,diate products for the manufacture of erythrene and its homologues.

The process for their'production consists O in treating ketonessuch as acetone and its homologues with tetramethyldiaminomethane either with or without condensing agents, such as caustic alkalis, alkali .carbonates' and bicarbonates, alkaline earths, aluminium hydrate, sodium phosphate. organic bases and salts. The condensation proceeds, although slowly, even at ordinary temperature and without condensing agents.

and the presence or absence of water or of.

cn3-co-c. R

are obtained by the two-fold introduction of the residue CH,,-N.(CH into the corresponding ketoneQ These ketodiamins can be separated from the ketomonoamins by fractional distillation.

Specification of Letters Patent.

Patented Aug. 19,1913.

application In order to illustrate the new process more fully the following examples are given, the parts being by weight Example 1P1=oduczz'0n 0f beta-acetylpropyZ-dz'methylamin and beta-beza-acet z Z- methg Zzrim-etkg Zenetezmmetlz-g ldiamin from tezmmeflzylcliamnomeflzrme and methyletizyllcezona-75O parts of aqueous formaldehyde (40 per cent.) are gradually dropped into 1350 parts of an aqueous dimethylamin solution (58.77 per cent.) care being taken to stir well and cool during this operation and 2500 parts of methylethylketone and 100 parts of caustic soda lye (l per cent.) are added to the solution of tetramethyldiaminomethane thus obtained. After this solution has been heated to 30 C. for about 20 days the pungent smell of tetramethyldiaininomethane has disappeared. The light red solution is saturated with carbonic acid or bicarbonate is added to it, the bases, and the excess of methylethylketone are separated and dried with pot-ash. separated from each other by a fractional distillation in 'vacuo. In this way about 700 parts of beta-acetylpropyldimethvlamin and 100 parts of beta beta acetylmethyltrimethylenetetramethyldiamin are obtained.

The same products but with a considerablysmaller yield are obtained by boiling under a reflux condenser for 4 days equal molecules of ethylmethylket-one and pure tetramethyldiaminomethane of the boiling point' Example 2-P10ductz'0n 0f betaa-cetg leflag Mimethg lamin and bem-acetg Ztfimeflzg Z- enezczmmethy Zaiamn from tetramethg Zdiaminomeflza'ne and a0et0ne.7 50 parts of aqueous formaldehyde (40 per cent.) are gradually dropped into 1530 parts of aqueous dimethylamin solution (58.77 per cent.) which is being stirred and cooled and 2000 The two bases are parts of acetone, 100 parts of baryta Water (saturated at ordinary temperature) and 500 parts of water are then added. After 20 days heating from 25 to' 30 C. bicarbonate is added to the brown solution in order to remove the baryta. Barium car-- bonate is removed by filtration. The oil is separated with potash from the filtrate, dried.

and is worked up as described in Example 1.

About 700 parts of the mixture of crudebases boiling" at from 50 to 98 C. (19 mm.) are obtained, containing 80 per cent. of betaacetylethyidiniethylarnin and 20 per cent. of beta-aoetyltrimethylenetetramethyldiamin.

The present application is a division of our prior application Serial No. 724,685.

1. Process for producing keto compounds containing the radical:

Which process consists in first treating a ketone with a tetramethyldiaminomethane compound and then isolating the keto compounds produced, substantially as described.

containing the radical: 20

Which process consists in first treating a ketone With a tetramethyldialninomethane compound With the addition of a condensing agent and then isolating the keto compound produced, substantially as described.

In testimony Whereof We have hereunto set our hands in the presence of two subscribing" 3.0

Witnesses. I

GEORG MERLING. [L. s.] HUGO KOHLER. [13. 8. Witnesses:

HELEN Norm, ALBERT NUFER. 

